A wide variety of thermosetting resins is well known in the art and the resins and cured products therefrom are useful in a variety of applications, particularly coatings, where properties of strength, toughness and solvent resistance are desired. Particular applications are in the automotive and lacquer industries where good adhesion and temperature stability are particularly important along with solvent and stress resistance.
Also known in the art is the class of linear alternating polymers of carbon monoxide and olefin(s) known as polyketone polymers or polyketones. An early production of such polymers is disclosed by Nozaki, for example U.S. Pat. No. 3,694,412, in which polymerization is conducted in the presence of arylphosphine complexes of palladium moieties as catalyst and certain inert solvents. More recent processes for the production of such polymers are illustrated by a number of published European Patent Applications Nos. including 121,965, 181,014, 213,671 and 257,663. These processes typically employ a catalyst composition formed from a compound of palladium, cobalt or nickel, the anion of a strong non-hydrohalogenic acid and a bidentate ligand of phosphorus, arsenic or antimony. The scope of the polymerization process is extensive but, without wishing to be limited, preferred catalyst compositions are formed from a palladium compound such as palladium acetate, the anion of a non-hydrohalogenic acid having a pKa below 2, e.g., the anion of trifluoroacetic acid or p-toluenesulfonic acid, and a bidentate ligand of phosphorus such as 1,3-bis(diphenylphosphino)propane or 1,3-bis[di(2-methoxyphenyl)phosphino]propane. The linear alternating polymers are typically materials of relatively high molecular weight but by control of reaction conditions, particularly reaction time and temperature, low molecular weight polymers, also termed oligomers, are alternatively produced.
It is known that reaction with amino materials will serve to modify the chemical structure of the polyketone polymers. In U.S. Pat. No. 3,979,374 there is disclosed the reaction of a linear alternating polymer with primary amine compounds to produce thermoplastic polymers having pyrrole moieties within the polymer chain. In copending U.S. patent application Ser. No. 138,768, filed Dec. 29, 1987, there is disclosed a class of polypyridines produced from polyketone polymers which are also thermoplastic.
A somewhat different type of product is also disclosed in U.S. Pat. No. 3,979,374 when a relatively high molecular weight polyketone polymer was reacted with hexamethylenediamine. The insolubility of the resulting polymeric product in hexaflurooisopropanol indicated that some degree of crosslinking was obtained when the polyketone polymer reacted with the difunctional amine. The crosslinked composition proved quite difficult to handle and the large amount of solvent needed to dissolve the polymer gave solutions of a composition too low to be useful from practical considerations. It would be of advantage to provide improved crosslinked resins which are thermosetting and which are produced by reaction of polyketone-type polymers and polyamino compounds.